Troll bosses? Really? Most Annoying Bosses wasn't relatable enough for the members of this forum?
In any case I'd put The Sorrow as one of mine. Yes I know I killed 100 people by shooting them between the legs but it was only because after covering them with bullets that was the only fatal hit. Also they shot me first - I have no regrets. >:[

Silver the Hedgehog from Sonic 2006. If you can't relate, you should be thankful. He is, in my experience, the worst boss in the history of gaming, by the simple fact that the gameplay is seriously broken and it is nearly impossible to beat him your first time. Sega are the real trolls. Just look up a video of the gameplay (preferably Game Grumps, if you want the full jist of everything that goes on in your mind when you fight him) and you'll know what I mean.

Silver the Hedgehog from Sonic 2006. If you can't relate, you should be thankful. He is, in my experience, the worst boss in the history of gaming, by the simple fact that the gameplay is seriously broken and it is nearly impossible to beat him your first time. Sega are the real trolls. Just look up a video of the gameplay (preferably Game Grumps, if you want the full jist of everything that goes on in your mind when you fight him) and you'll know what I mean.

Blue from Pokémon. He's always one step ahead of you, bragging about how many Pokémon he's caught and how many badges he has. I had so much trouble beating the Elite Four, but I eventually succeeded, only to be told that piece of $%&* was still left to beat. And, yes, he did beat me on my first try. Blue is just an all round douchebag troll.

Blue from Pokémon. He's always one step ahead of you, bragging about how many Pokémon he's caught and how many badges he has. I had so much trouble beating the Elite Four, but I eventually succeeded, only to be told that piece of $%&* was still left to beat. And, yes, he did beat me on my first try. Blue is just an all round douchebag troll.

That dude with the Machine gun in who you faced before your Brother at the end of Double Dragon was a bit of a troll.
But the ultimate troll in that game were those bloody square pillars that pushed out of those grey walls in the final stage that had NO pattern.

Currently Playing: Chip 'n Dale Rescue Rangers! - NES
We shall swim to Bubble Island, or you will suffer the wrath of my Trident Laser!
80s FANATIC & King of NES Tekkidome!